This post reveals stylist’s secrets how to style leather shorts for work and play at any age.

  1. Who said women can’t wear shorts at any age?
  2. Can you wear shorts at work?
  3. How to style shorts for Casual Friday
  4. Try a summer weekend look with shorts, a shirt and sunnies
    • Complimentary colors are great for chic outfits
  5. How to style shorts for date night?
  6. How to wear shorts in winter?
  7. Shorts with outerwear
  8. In a nutshell

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Who said women can’t wear shorts at any age?

Here is my short story about shorts. Why is it that there are so many articles in prominent newsletters and magazines that say “Don’t wear shorts after age of 30, 40, ….” (you add the number here).

Isn’t it true that shorts look awful and frumpy at any age when they are not styled? And isn’t that true for all clothes?

Style your shorts at any age. #agelessstyle Click To Tweet

Like with other clothing leather clothes have to be styled to look great. You can find a guide how to wear leather over 40 in the post at the link.

midlife blogger in leather shorts, Hawaiian shirt and leather baseball cap
Oliveo leather shorts and Vintage Silk Hawaiian shirt, LeatherCoatsEtc leather baseball hat, Paloma Picasso sunglasses, espadrilles sandals, Hermes collier de chien bangle, and DIY belt (all own) for a summer Saturday on the deck


We can wear what we can style. Click To Tweet

Can you wear shorts at work?

Short suits perennially have a moment. When your work dress code allows leather, and you love this version of pants, wear the trend. Suits with thigh-length pants are having a moment right now. Thus, we can even wear a fake leather shorts suit at the office when we style the it in a professional way. See the photo below for an faux leather shorts suit outfit inspiration.


short pants with white blazer and sweater, pantyhos
Ann Taylor blazer, Oliveo shorts, Brooks Brothers sweater, H buckle belt, Ray Ban aviator sunglasses, unbranded pantyhose and Harley Davidson booties (all own)
stylist in unmatched shorts suit with olive button-down shirt
Nine West booties, semi-opaque tights, Oliveo button-down shirt, blazer, Ray Ban sunglasses (all own)
over 50 years old street style blogger in shorts
Pippa bag, H buckle and belt, Hermes bangle, short sleeve blazer, gray Tee, Ray Ban purple mirrored glasses


Given the shorts suit trend, we even wear them to the office. #wearwhatyouwant Click To Tweet

How to style shorts for Casual Friday

The first outfit in this post is cute for the weekend, but would not work on Casual Friday at the office. Adding a blazer and pantyhose, ditching the baseball cap plus swapping the sandals for pumps, however, would give the entire outfit a suit-like vibe, and would make it office appropriate in a creative or casual work environment on Fridays.

The look below shows a Casual Friday winter look. In the cold time of the year, these trousers look best with opaque tights. The look is an example for the fake suit outfit idea.

style over 40 Shorts with blazer for the office
Oliveo leather shorts with GNW tights, GNW Luxe wool cashmere sweater, LV scarf, statement belt, Vittoria Verani blazer for a suit like vibe (all own)

Try a summer weekend look with shorts, shirt and sunnies

Sure, you can wear leather in spring and summer. It’s not just for winter. Especially, when the hide piece has the cut of a typical summer clothes. The black leather shorts, striped T-shirt and silk scarf are a comfortable, but chic outfit for a late dinner on the deck on the weekend.

Note the white nights allow to enjoy the Sun even late in the evening. This photo was taken after 2100 (9:30 pm).

In Alaska, nobody would tell their kids to come home when it gets dark. In summer, they would not see their kids for about 2 months. #Alaska #funfacts Click To Tweet
leather lady in leather shorts on straw baseball hat at the river
Oliveo leather shorts, The Limited striped Tee, Seiko watch, floral silk scarf, gold Madden Girl sandals, baseball style straw hat


The next weekend outfit inspiration shows the shorts with a striped T-shirt and a star denim jacket. I paired the look with black pumps and my Celine tote for a stroll downtown to enjoy the weather on a day off.


influencer in denim jacket, tigh long pants, stripped top

red, white, blue and black outfit
Weekend look details: Oliveo leather shorts with pumps, Star denim jacket, Hermes H-buckle belt, Hermes collier de chien leather band, Paloma Picasso sunglasses and unbranded striped T-shirt (all own)



Did you know that there is a guide what to look for when shopping for leather clothes right here on the blog? Check it out, to get the best.

Complimentary colors are great for chic outfits

In the next outfit, I paired a gingham blue and white button down shirt, orange bag and cork plateau orange sandals with the knee length pants. The plateau gives some height, while they are super-comfy and look relaxed. These sandals are less risky with shorts than high heels would be. The color combination is pulled from the color wheel. Orange is the complimentary color to blue, i.e. a great match. And, moreover, the Bavarians have a Lion as their mascot and lions are orange, right? Furthermore, white and black are complimentary colors. Thus, perfect for a multi-color outfit without looking like having fallen into a box of crayons.

Complimentary colors always make a great look. #styleadvice Click To Tweet

over 50 years old woman in leather shorts and straw hat

fashion blogger over 50 in mature look with shorts
Details of above weekend look: Blue and white Carhartt Gingham shirt, Oliveo leather shorts, Kieselstein Cord belt and 3 horses buckle, Hermes collier de chien bangle, Hermes enamel bangles, carved agate necklace and earrings, Tissot stone watch, Ray Ban sunglasses, orange Michael Kors patent leather sandals and D&Y straw baseball hat (all own)

How to style shorts for date night?

I am a fan of Bond movies. Ever since I watched Goldfinger, I was fascinated about golden clothing. Thus, when I saw these shorts on eBay, I had to buy this beauty. I love their high waist. It makes my legs look miles long.

Statement pieces like this golden pair are easiest to style with a neutral color to ground them. To not go overboard or look like trying too hard, it is best to choose a high cleavage. It keeps people guessing.


style book author in golden shorts

over 50 years old woman in golden leather shorts
Outfit details: Joeffer Caoc golden leather shorts with Great Northwest corduroy button-down shirt, GNW opaque tights, and Madden Mary Janes (all own)

How to wear shorts in winter?

It’s probably easier to pull off shorts in winter than summer when you can wear opaque tights underneath. Go with tights and shoes in the color of the trousers for a slim look and elongated leg.

fashion over 40 Leather shorts with tights
Oliveo leather shorts with GNW Luxe cashmere wool sweater, GNW tights, Harley Davidson booties, LV silk scarf, and smoky quartz flower buckle statement belt (all own)


The next winter look shows that you can wear shorts also with layers. Here a button-down shirt is layered under a thin sweater. Of course, when layering opaque tights are a Must to make the look work. Also pay attention to where the hems hit. The sweater is about 4 inch (10 cm) longer than the sweater. The sweater is worn untucked to avoid bulk. Make sure that enough of the pants’ legs remains visible.  It’s all about getting the balance right.

tight high pants with layering tops
Outfit details: Oliveo leather shorts, GNW tight, white Fossil denim jacket, Oliveo plaid button-down shirt, baroque pearl necklace, Hermes collier de chien bangle, Ann Taylor cashmere sweater, Kieselstein Cord belt and buckle, and pumps (all own)


short suit
Outfit details: Oliveo leather shorts, GNW tight, white Fossil denim jacket, Oliveo plaid button-down shirt, baroque pearl necklace, Hermes collier de chien bangle, Ann Taylor cashmere sweater, Kieselstein Cord belt and buckle, and pumps (all own)

Shorts with outerwear

Make sure that your coat is several inches longer than the trousers not only to stay warm in winter. It just looks like you forgot to put on pants or a skirt when you wear short shorts and a jacket that ends at the hem of them. Looking weird is never in style.

mature winter outerwear look
Chocolate brown shearling coat styled with hat, and LeatherCoatsEtc tan gloves (all own) worn over the pink sweater winter outfit shown earlier in this post


The next outerwear inspiration has the plaid with sweater outfit underneath.

denim jacket, tights, short trousers, plaid shirt outfit
LeatherCoatsEtc gloves, Shearling coat, Salamander shearling booties, Michael Kors leopard print bag, blanket scarf, Kieselstein Cord belt with ethnic buckle, and vintage hat (all own). This outerwear is worn over the layered outfit. The pumps are only worn at the office inside.


You can find five further tips to style your outerwear to avoid winter boredom at this link.

In a nutshell

You can wear leather shorts at any age year round when you style them. Another important point is to only wear high quality leather to not look cheap or trashy.

The End of this short(s) story.

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Photos: G. Kramm

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